rel-(2R,6S)-4-[2,3-Dihydro-2-(phenylmethyl)-1H-isoindol-5-yl]tetrahydro-2,6-dimethyl-2H-pyran-4-ol → (2S,6R)-4-(2,3-Dihydro-1H-isoindol-5-yl)-2,6-dimethyl-tetrahydro-pyran-4-ol

HRID 225650Notes

Reaction equation

HRID 225650 reaction equation
C([N:8]1[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([C:17]3([OH:25])[CH2:22][C@@H:21]([CH3:23])[O:20][C@@H:19]([CH3:24])[CH2:18]3)[CH:14]=2)[CH2:9]1)C1C=CC=CC=1.[H][H]>>[CH2:9]1[C:10]2[C:15](=[CH:14][C:13]([C:17]3([OH:25])[CH2:22][C@@H:21]([CH3:23])[O:20][C@@H:19]([CH3:24])[CH2:18]3)=[CH:12][CH:11]=2)[CH2:16][NH:8]1

Participants

3

Reactant 2

HCID 57753466rel-(2R,6S)-4-[2,3-Dihydro-2-(phenylmethyl)-1H-isoindol-5-yl]tetrahydro-2,6-dimethyl-2H-pyran-4-olHCID 178418361HCID 178418361, compound

Product 1

HCID 57753310(2S,6R)-4-(2,3-Dihydro-1H-isoindol-5-yl)-2,6-dimethyl-tetrahydro-pyran-4-ol

Procedure

Prepared in analogy to Example A62(c) from (2S,6R)-4-(2-benzyl-2,3-dihydro-1H-isoindol-5-yl)-2,6-dimethyl-tetrahydro-pyran-4-ol and hydrogen. Brown oil. MS (m/e): 248.3 ([M+H]+, 100%).

Sources & evidence

ORD record
ord-ea0e9923eca147f1b16fa884529576bb
Source dataset
uspto-grants-2009_07
Patent number
US07557114B2

Reaction notes

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